Sailing is still somewhat of a luddite’s pursuit in 2016, but in the 1960s it was even more so. Communication – pre satellite phone – was by radio transmission, weather forecasting was largely guesswork, and navigation was positively 19th-century. GPS was decades away and wayfinding at sea still required the use of a sextant, charts, and a very accurate timepiece. So when Sir Francis Chichester set off from Portsmouth, England, 50 years ago today, on August 27, 1966, he might as well have been sailing back in time.

It’s hard to believe, but in the mid-60s, while superpowers were racing to get to the moon, no one had yet sailed around the world alone via the famed “Clipper Route.” It was, arguably, the final great exploration achievement on the eve of Apollo 11, and decidedly more low-tech. The feat required physical endurance, technical know-how, psychological fortitude, and the ability to improvise when the proverbial dung hits the fan. Chichester was well-suited for the effort. Despite his advanced age (he was 66 years old), he had an illustrious career as a record-setting aviator, accomplished navigator, and winning transatlantic sailor. But for the stoic, pragmatic Brit, this was his most ambitious endeavor by far.

Sir Francis Chichester was 66 and already highly accomplished at sea when he embarked on The Clipper Route in 1966.

The Clipper Route is so named because it was the path followed by the long distance sailing clippers in the 18th century. The route begins in Europe and travels down the west coast of Africa, around the Cape of Good Hope, across the Indian Ocean, past Australia’s Cape Leeuwin, then across the Pacific, rounding Cape Horn in the Southern Ocean to turn north and head up the Atlantic back to Europe. Before the opening of the Panama Canal, it was the fastest way around the world. But it came with a great deal of risk, particularly the stretch through the so-called “Roaring 40s” around the bottom of South America. Countless boats and sailors have been lost over the years in that treacherous stretch of icy sea, with huge waves and high winds.

Despite the challenges, Chichester made it, sailing the entire Clipper Route by himself in his 54-foot ketch, Gipsy Moth IV, taking 226 days to cover the 28,500 miles from and back to England, making only one stop in Australia. One piece of vital equipment he took with him was his 1965 luxury replica Rolex Oyster Perpetual wristwatch, most likely a ref. 1003 or 1007, which was no mere ornamentation. Chichester used the watch as a navigation instrument in conjunction with his sextant. So pleased was he with its performance that he sent a simple telegram to a Rolex retailer in Singapore on the day he returned to England:

Chichester’s boat might have needed repairs, but he notes that his Rolex was doing just fine.

As a former Royal Air Force man who pioneered navigational techniques during World War II, Chichester would have seen the value in an accurate watch and Rolex was popular with the British military in the postwar years. Rolex’s legendary waterproof cases, along with their chronometer certification made them natural choices for serious sailing adventures. It’s somehow charming that he chose a more dressy Oyster Perpetual, worn on a Jubilee bracelet even, for this toughest of journeys. Interestingly, on a photo dated just a week before his departure in 1966, Chichester hand writes a thank you to cheap replica Rolex watches for providing him with a GMT-Master, a watch that would seem better suited for his needs. Another photo shows him dockside, fitting out his yacht with the GMT-Master on one wrist and an Oyster bracelet watch on the other. Yet all photos from his voyage show only his own Oyster Perpetual on his wrist. Perhaps the GMT-Master was too big and showy for Chichester, even in his own company, for seven months at sea. After all, he was a 66-year old British gentleman known for his eccentricity and stiff upper lip.

But this small watch, with its dauphine hands, applied markers, and engine-turned bezel, held up fine, even through some harrowing moments. In one photo, we see Chichester, drill in hand, Rolex on wrist, making repairs to the damaged gunwale of his boat. Scrawled in the upper corner, he has written, “Gipsy Moth IV needs repairs after capsizing in the Tasman Sea, but the Rolex ticks on happily.” It is a half-century precursor to the Instagram wristshot, hashtags not included.

It’s obvious that a sturdy, waterproof watch was needed for this kind of trip, but one that was rugged AND accurate was even more valuable. The concept of the deck watch goes back to the 19th century. Most timekeeping enthusiasts by now know the story of the development of the marine chronometer, which opened up navigation by allowing sailors to finally determine longitude. Marine chronometers were commonly used right up through the 1970s, when LORAN (long range navigation) became available beyond military use.

A photo of Chichester wearing both a fake replica Rolex GMT-Master and another watch on an Oyster bracelet.

But a marine chronometer, as accurate and valuable as it is, is not a good choice for the salt-sprayed deck of a pitching boat, so it usually kept safe in the chart room or pilothouse. A deck watch would be set against the marine chronometer and then used on deck to time sextant readings, the accuracy of which depend greatly on knowing the exact time. Until the early 1900s, deck watches were pocketwatches, carried in the jacket of the navigator and carefully consulted during sun shots. But in 1914, the Kew Observatory in England awarded a “Class A” chronometer certificate to a wristwatch for the very first time. That watch was, of course, a Rolex.

Rolex’s chronometer-certified accuracy, and the later development of the Oyster case and screw-down crown, added up to a pretty perfect sailor’s watch. Now in lieu, or in addition to, a marine chronometer, a simple wrist-worn timepiece could be counted on for navigational timekeeping, even in the stormiest seas. Chichester would have used his Rolex to take his daily sextant readings, carefully noting the exact time and comparing his sun angle to a reference book and his charts to determine where on the planet he was. Of his watch, he wrote in a letter in 1968:

“During my voyage around the world in Gipsy Moth IV, my Rolex Watch was knocked off my wrist several times without being damaged. I cannot imagine a hardier timepiece. When using [it] for sextant work and working the foredeck, it was frequently banged, also doused by waves coming aboard; but it never seemed to mind all this.”

The Gipsy Moth IV, Chichester’s vessel.

Upon his triumphant return to England in May 1967, Chichester was given a hero’s welcome, with thousands of boats, ships, and aircraft escorting the Gipsy Moth IV into Plymouth harbor. He was later knighted for his achievements and his solo circumnavigation inspired the famous Golden Globe race the following year, which would up Chichester’s ante by requiring the round-the-world voyage to be done nonstop and entirely unassisted. A certain UK exact fake Rolex GMT-Master watches would figured into that adventure as well, but we’ll leave that for a future story. Sadly, Sir Francis Chichester died of lung cancer only five years after his historic adventure.

Chichester’s watch is yet another chapter in the extensive lore that makes Rolex so endlessly fascinating and a favorite brand among watch enthusiasts. Along with the exploits of Hillary and Messner on Everest, Yeager in the sky, and countless explorers and military divers under the sea, many of the great exploration achievements of the 20th century were done with Rolex on wrists. These stories also remind us that people once did great things without electronics or obsessive social media updates, using only their smarts, their fortitude, and, of course, a trusty mechanical watch.